Method for preparing phenylpentachloro-ethane



Patented Detail, 1945 f NI ED STA ES PATENT" t-me a 12,890,629 a 1 MITHODFORPBEPARINGPBENYL- PENTACHLOBO- vlrm Weinmayr, Pitman, N. 3., unmito n. I. du Pont de Nemours & Company, Wilmington,

DeL', a corporation'ol Delaware I No Drawing. Application December 8, 1943,

' Serial No. 513.419

s can... (Cl. 266-651) This invention relates to new processes for the preparation of phenyl-pentachloro-ethane, and

especially to processes of preparing the compound from alpha-trichloro-acetophenone.

Phenyl-pentachloro-ethane was prepared from ethyl benzene by H. Blitz [Annalen 296, page 271 (1897) l. The method is circuitous and in general it is unsatisfactory for the manufacture of. the compound except on a laboratory scale.

It is, therfore, an object of this invention to provide methods for the preparation of-phenyl- The product distills at'llo'o. under l mm. pressure' and has a crystallizing point or C. v when molten, the product is a colorless clear liquid.

alpha-trichloro -acetophenone'mav be prepared,

by heating a of benzene, trichloro-acetylchloride and anhydrous aluminum chloride at about -45 C. until the evolution oi hydrochloric acid has practically; stopped, and then. recovering the product from a.' benzene layer ,which forms upon drowning-the resulting reacpentachloro-ethane from readily available start- 7 ing materials. Another object of the invention is to provide processes which can be carried out easily on a large scale by the use of readily avail able plant equipment. Other objects of the invention will be apparent from the following description.

These objects are accomplished by treating.

alpha-trichloro-acetophenone with phosphorus pentachloride at elevated temperatures'and sep- -aratina the product from thereaction mixture reaction is represented by-suitable means.- The by the equation JB-w.

+ Pm O-QOI: root In view of the known labile character of the tion mixture in ice. Aipha-trichloro-aoetophenohe thus'obtained has a boiling point of C.

- at 1 mm. pressure.

Phenyl-pentachloro-ethane has been'found to be especially useful as an intermediate from which'various-other novel and useful organic compounds can be prepared.

Instead of carrying gout the process at,

C.-and allowing the phosphorus oxychloride to distill, the process can be carried out under from the reaction mass by distillation at distillation temperatures. The best yieldsare obtained when a considerable excess of available chlorine chlorine atoms in alpha-trichloro-acetophenone, it was surprising that no side reactions or decompositions took place under the drastic reaction conditions hereinafter set forth, and that a conversion approaching near to quantitative conversion to phenyl-pentachloro-ethane could be accomplished.

The invention will be more fully set forth in the following more detailed description whichin- .cludes examples that are given as illustrative embodiments of the invention and not as limitations thereof. Parts are expressed inputs by weight unless otherwise noted.

' Example six hundred and ten parts of alpha-trichloroacetophenone and 900 parts of phosphorus pentachloride are heated to l70-180 C. for 24 hours.- 7 The phosphorus oxychloride which forms during this P riod is allowed to distill 01!. The reaction mass is then poured on ice containing 750;;

parts oi carbon tetrachloride. The resulting solution of 'phenyl-pentachloro-ethane is washed acid-tree, dried, and distilled. Seven hundred parts or phenyl-pentachlom-ethane are obtained.

reflux, in which case distillation temperatures at least as highas about 120 C. can be used. Equivalent amounts 0! phosphorus trichloride and chlorine can be used in the reaction mixture instead of phosphorus pentachloride. If desired, the phenyl-pentachloro-ethane can be separated is present in the form of phosphorus pentachloride or its equivalent.

This is a continuation in application Serial No., 413,167; Patent No. 2,351,247. l

From the foregoing disclosure it will be recognized that the invention is susceptible of modification without departing from the spirit and scopethereof anditistobeunderstood thattheto about 180 C. and the mmwcunn mid inning minin to rromthcrcectionmiztum, H L'Ihcproocssinaccordanccwithci'oim-Iin which thc reaction mixturais hcatedto a temperature at least as high as about 120? 0.15misumoient to reflux the phosphorus oxychioride gamcao 'lflnawoccssincccordmcewithclaimiin which the phosphorus pentachioride is formed in tho reaction mm by adding phosphor-m :txichioridc and chlorine to the reaction mixture 5 in, mounts :uflicicnt to form phosphorus penta- 

